Sodium Carbonate → Methyl 4-(3-((4-(trifluoromethoxy)phenyl)carbamoyl)phenyl)thiophene-2-carboxylate

HRID 629055노트

반응식

HRID 629055 반응식
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([C:35]([O:37][CH3:38])=[O:36])[S:33][CH:34]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:16][C:15]([F:18])([F:17])[O:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5]([C:4]2[CH:3]=[C:2]([C:30]3[CH:31]=[C:32]([C:35]([O:37][CH3:38])=[O:36])[S:33][CH:34]=3)[CH:21]=[CH:20][CH:19]=2)=[O:6])=[CH:9][CH:10]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 13710333-bromo-N-(4-(trifluoromethoxy)phenyl)benzamideHCID 52911233Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate

생성물 1

HCID 72202880Methyl 4-(3-((4-(trifluoromethoxy)phenyl)carbamoyl)phenyl)thiophene-2-carboxylate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

A mixture of 3-bromo-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 3.1, 50 mg, 0.139 mmol in 2.4 mL DME), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (0.180 mmol), 2 M Na2CO3 (0.104 mL, 0.208 mmol), water (0.8 mL), and (Ph3P)4Pd (8 mg, 6.94 μmol) in a sealed vial were subjected to MW irradiation at 150° C. for 10 min. The RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL), the cartridge was washed with MeOH (10 mL) and the combined filtrates were evaporated to dryness under reduced pressure to give the crude product was purified by preparative HPLC to afford the title compound. UPLC-MS (Condition 6) tR=2.37 min, m/z=422.3 [M+H]+.

후처리

  1. customvial were subjected to MW irradiation at 150° C. for 10 min
  2. filtrationThe RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL)
  3. washthe cartridge was washed with MeOH (10 mL)
  4. customthe combined filtrates were evaporated to dryness under reduced pressure
  5. customto give the crude product
  6. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-34af188d1f53429d9692372f75369aff
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315489B2

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